Methanesulfonyl chloride → HCID 46917725, compound

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Reaction Steps

To a solution of N1-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N3,N3-dimethyl-N1-(3-piperidinyl)-1,3-propanediamine (155 mg, 0.28 mmol) and DIPEA (1 mL) in CH2Cl2 (10 mL) was added methanesulfonyl chloride (0.5 mL) at 0° C. The resulting mixture was stirred for 16 hrs at room temperature. After dilution with water, the organic layer was separated, and the aqueous layer was further extracted with CH2Cl2 (3×15 mL). The combined organic fractions were dried over Na2SO4, and the solvent removed under vacuum. The residue was chromatographed on alumina eluting with CH2Cl2/MeOH (97:3) to give partially pure material, which was further purified by chromatography on silica eluting with CH2Cl2/MeOH (97:3) to give N1-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N3,N3-dimethyl-N1-[1-(methylsulfonyl)-3-piperidinyl]-1,3-propanediamine (125 mg, 72% yield).

Provenance & Evidence